1-Methylpyrrolidine → N-(4-((6-(3-pivaloylureido)pyridin-3-yl)oxy)pyridin-2-yl)pyrrolidine-1-carboxamide

Participants

Reaction Steps

A mixture of Example C2 (0.163 g, 0.394 mmol), pyrrolidine (0.028 g, 0.394 mmol) and N-methylpyrrolidine (0.017 g, 0.197 mmol) in dioxane (3 mL) was heated at 80° C. for 45 min, cooled to RT, and concentrated to dryness. The residue was suspended in MeCN and the mixture was sonicated for a few minutes. The light beige solid was collected by filtration, washed with MeCN and dried overnight at 80° C. to provide N-(4-((6-(3-pivaloylureido)pyridin-3-yl)oxy)pyridin-2-yl)pyrrolidine-1-carboxamide (0.118 g, 67%). 1H NMR (400 MHz, DMSO-d6): δ 11.22 (s, 1H), 10.44 (s, 1H), 8.72 (s, 1H), 8.23 (d, J=2.9 Hz, 1H), 8.13-8.04 (m, 2H), 7.71 (dd, J=9.0, 2.9 Hz, 1H), 7.47 (d, J=2.4 Hz, 1H), 6.60 (dd, J=5.7, 2.4 Hz, 1H), 3.39-3.30 (m, 4H), 1.84-1.71 (m, 4H), 1.21 (s, 9H); MS (ESI) m/z: 427.2 (M+H+).

Provenance & Evidence